The 8 Best Documentaries About Waylon Jennings

Nov 19, 2023 | Best Of, Celebrities, Music

The legendary Waylon Jennings is one of the most influential country music artists of all time. His influence can still be heard in today’s country music and his memory will live on forever. But, while we may never experience a live performance of his classic songs again, there are other ways to appreciate the life and works of this iconic artist. Enter: documentaries about Waylon Jennings. These documentaries tell the story of his life, music, and influence with stunning visuals and insightful interviews. Read on to learn about some of the best documentaries about Waylon Jennings that you can watch today!


1. Waylon Jennings – “My Heroes Have Always Been Cowboys

Growing up, I remember my dad playing Waylon’s music in his S10 Chevy as we drove down the highway. His songs were full of life and joy, but also packed with heartache and understanding of the female experience. Every time I hear one of his songs, it feels like he’s right there with me – singing along and telling jokes. The memories created while listening to Waylon Jennings will stay with me forever. His music was and still is a part of my life, and his songs provide an escape from the everyday. Whether you’re feeling heartbroken or just want a good laugh, Waylon’s music is sure to make it better.


2. Waylon Jennings Life Story- Documentary

Waylon Jennings was a legendary country music star who rose from humble beginnings in Littlefield, Texas to become one of the biggest names in Nashville and beyond. From his early days learning guitar from Buddy Holly to his Outlaw years, Waylon’s life story is as captivating as it is inspiring.This documentary tells the remarkable tale of how a young man with big dreams and a unique voice created an unrivalled legacy in country music. It showcases the highs and lows of Waylon’s career, featuring interviews with his family, friends, and musical peers who all help to provide perspective on his journey.



Waylon Jennings was a man of many talents, and his life story is one that should be shared with everyone. That’s why we need to talk about the CMT Inside Fame documentary. This episode offers an in-depth look at the career and life of Waylon Jennings. Through interviews with friends, family, industry staff, and more, viewers will get to know the life of the legend that was Waylon. The episode includes exclusive interviews with his wife and children, as well as behind-the-scenes footage from some of Waylon’s biggest performances. Hear first hand about his career milestones and successes.


4. Waylon Jennings & Willie Nelson – The Outlaw Movement in Country Music Full Episode!

Willie Nelson and Waylon Jennings were the two forces that started the country music Outlaw Movement. This movement pushed boundaries in genre by introducing elements of rock, blues, jazz, and folk into their sound. The album “Wanted: The Outlaws” was the catalyst for this transformation. It featured songs like “Good Hearted Woman”, “Luckenbach, Texas” and “Mammas Don’t Let Your Babies Grow Up To Be Cowboys”. The Outlaw Movement put forth a rebel attitude to their music that was revolutionary during the time.


5. Waylon Jennings Stories

Be enthralled by the tales of Waylon Jennings from those who knew him best. Kenny Vaughan, Dave Roe, Chris Scruggs, Tim Carroll and Barry Walsh share their stories about the country music icon that have never before been heard. Listen to these special accounts of touring with Waylon as they remember his unique talents and original style. Get up close and personal as they speak candidly of the beloved singer and songwriter. Relive a legendary era with these breathtaking tales from those who knew Waylon Jennings best. It’s an experience like no other, so dive into the stories that make up the legend.


6. Waylon Jennings Interview Part 1, American Singer-Songwriter & Country Music Outlaw

Waylon Jennings is an iconic figure in American country music and his influence continues to echo years after his passing. This episode of NPT’s A Word on Words with John Seigenthaler delves into the history of country music, exploring Waylon’s experience as a part of the Outlaw Movement. The singer-songwriter also shares personal stories about his beloved wife, Jessi Colter, and the book “Waylon” he wrote in 1996. Never before seen footage from this interview is pulled from NPT’s archives to bring viewers a unique perspective on the legacy of Waylon Jennings. Don’t miss this part 1 of 2 look into the life of an American music legend!


7. Waylon Jennings Inside Fame

Waylon Jennings: Inside Fame is a feature-length documentary that sheds light on the life and career of one of country music’s biggest icons. Produced by CMT, this eye-opening film follows Waylon’s journey from his early days in Amarillo, TX to his emergence as an international celebrity. Through interviews with family, friends, and collaborators, Waylon Jennings: Inside Fame provides an intimate view of this legendary singer-songwriter’s story. From his rise to fame, his relentless drive and passion for music, and his influence on generations of artists that followed him, Waylon Jennings: Inside Fame is a must-see look into the life of one of country music’s most influential figures.


8. Country History X: Waylon Jennings and the Cocaine Bear (#6)

Country History X: The Rags to Riches Story of Waylon Jennings The story of music legend Waylon Jennings is one that transcends time and place. From his humble beginnings as a poor but talented singer-songwriter in Texas, he went on to become an international icon in the country music world. But his journey wasn’t without its bumps along the way. His relationship with drugs, specifically cocaine, is one that will continue to be discussed for years to come. This documentary takes a closer look at Waylon’s life and his struggles with addiction through interviews, re-enactments of key events, archival footage, and more.

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David B